Bruno richard seifert



UNITED STATES* PATENT OFFICE.

BRUNO 'RIOI-IARD SEIFERT, on RADEBEUL, GERMANY, AssIcNoR To THE CIIEMISOHE FABRIK VON IIEYDEN, GESELLSOIIAFT MIT BESOIIRANKTER IIAFTUNG, OF SAME PLACE.

ISOHOMOVANILLIN.

SPECIFICATION forming part of Letters Patent N 0. 575,070, dated January 12, 1897.

I Application filed June 6, 1896. Serial No. 594.697. (Specimens) To all whom it may concern.-

Be it known that I, BRUNO RICHARD SEI- m FEET, ofRadebeul, nearDresden, in the Kingdom of Saxony, German Empire, have in 5 vented and produced a new Group of Aromatie Substances, of which the following is a specification.

Ilomovanillins have been produced which differ frgom vanillin con; 5 c n ocn l on 2 in this, that they contain instead of the group OOII the homologous groups OO II Ot il These known homovanillins have the geucral formula OOll I have produced and my invention consists in a hitherto-unknown group of aromatic sub stances diitcring from the above homovanil- 7 in which the general group Il d-l. may be replaced by the special groups 01 I and C ll The isolunnovan-illins have an extremely permanent smell or scent similar to vanillin, but distinctly differing from the same. They are easily soluble in soda-lye and in ether and more diflicultly soluble in alcohol. They crystallize out of hot alcohol in colorless or yellowish scales and needles. v

The isohomovanillin OOH. l OH 2 lu 2 (J-[3 L (30H 5 melts at 165 centigrade, the ethylisohomovanillin Y ()G ll 1 c u on CH 4 con 5 at 91 centigrade. These isohomovanillins may be produced in different ways-for instance, by the action of chloroform on isohomopyrocatechinether of the formula OC,,II -1 1 ll OH 2 CIT 4 or also in another manner.

From the isocrcosol, for example, described by Tiemann and Koppe, Berichic der Deutoou 1 cm, on '2 on i the isohomovanillin is obtaincdin the following manner: Ten kilograms of isocreosol are dissolved in thirty kilograms of soda-lye, of. which each kilogram contains four hundred and thirty'grams of sodiumhydroxid, and in thirty-seven kilograms. of water; Into this 9c solution, which is heated in the water-bath,

fifty kilograms of Clll0l'0f0l'lILil-l'0 caused'to flow. After the latter has been consumed by the reaction the solution is allowed to cool down and treated with diluted muriatic acid and extracted with ether. From this other solution the aromatic substance is extracted by means of a solution of bisultite. of sodium.

13y the addition of acid the bisuliitc compound is decomposed. The aromatic sub- :00

stance thus liberated separates in solid form. It is Withdrawn byimeans of filtration and purified by recrystallization out of alcohol.

If instead of isoereosol the equivalent quantity of the ethylhomopyroeateehin 00 1i 1 (7 1i Oil 2 on, 4 is used, the ethylisohomovanillin 00 1i, '1 Z ()ll 2 on, i COM 5 is obtained. The proportions of concentration and of quantity mentioned in this ex ample may vary within wide limits, and. instead of the soda-lye other alkalies or earth aikalies may be employed, also instead of water other dissolving liquids.

W hat I claim as my invention is The new aromatic substances obtained from isoereosol and similar bodies and heroin termed isohomovanillins of the formula ()U ll -tl 1 ()II' 2 (3] I, -L (101]. 5

whereby the general group C li +l is limited to the special cases CH and 0 1i, the said 'isohomovanillins being soluble in soda-lye, 

